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[ CAS No. 13143-47-0 ] {[proInfo.proName]}

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Chemical Structure| 13143-47-0
Chemical Structure| 13143-47-0
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Product Details of [ 13143-47-0 ]

CAS No. :13143-47-0 MDL No. :MFCD06659526
Formula : C11H10N2O Boiling Point : -
Linear Structure Formula :- InChI Key :LXFHLDJQBIZFOP-UHFFFAOYSA-N
M.W : 186.21 Pubchem ID :11535695
Synonyms :

Calculated chemistry of [ 13143-47-0 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.0
Num. rotatable bonds : 1
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 56.44
TPSA : 48.02 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.72
Log Po/w (XLOGP3) : 1.27
Log Po/w (WLOGP) : 1.43
Log Po/w (MLOGP) : 1.59
Log Po/w (SILICOS-IT) : 1.36
Consensus Log Po/w : 1.47

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.807 mg/ml ; 0.00434 mol/l
Class : Soluble
Log S (Ali) : -1.88
Solubility : 2.47 mg/ml ; 0.0133 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.27
Solubility : 0.101 mg/ml ; 0.000542 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.65

Safety of [ 13143-47-0 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 13143-47-0 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 13143-47-0 ]
  • Downstream synthetic route of [ 13143-47-0 ]

[ 13143-47-0 ] Synthesis Path-Upstream   1~4

  • 1
  • [ 53427-97-7 ]
  • [ 13143-47-0 ]
YieldReaction ConditionsOperation in experiment
86% With water; ammonium chloride; zinc In tetrahydrofuran In a 100 mL round bottle, 1-(4-nitrophenyl)pyridin-2(1H)-one (1.0 g, 4.63 mmol, Eq: 1.00) and zinc (1.51 g, 23.1 mmol, Eq: 5.00) were combined with a solution of saturated NH4Cl aqueous solution/ THF (1:1) (50 ml), the mixture was stirred at for overnight. Filter out the solid, extracted with CH2Ch (50 mLx2), the organic layer was dried over anhydrous Na2S04; the solution was concentrated under vacuum to afford the crude product 740 mg (86percent). MH+ 188.3
79% With water; ammonium chloride; zinc In tetrahydrofuran; methanol at 20℃; Synthesis of 1-(4-Amino-phenyl)-1H-pyridin-2-one
Ammonium chloride (4.45 g, 83.26 mmol) in water (10 mL) and methanol (20 mL) was added to a stirred solution of 1-(4-nitro-phenyl)-1H-pyridin-2-one (1.8 g, 8.3 mmol) in THF (20 mL).
Zinc powder (4.3 g, 66.6 mmol) was then added portion wise and the resulting mixture was stirred at room temperature for 30 minutes.
The mixture was filtered over celite and the filtrate was concentrated and extracted with ethyl acetate.
The organic layer was washed with brine solution, dried over Na2SO4 and concentrated to afford 1.23 g (79percent) of 1-(4-amino-phenyl)-1H-pyridin-2-one. 1H NMR: (DMSO-d6): δ 7.6-7.4 (m, 2H), 7.0 (d, 2H), 6.7 (d, 2H), 6.45 (d, 1H), 6.3 (t, 1H), 5.4 (s, 2H).
Reference: [1] Patent: WO2014/135471, 2014, A1, . Location in patent: Page/Page column 98
[2] Patent: US2009/239848, 2009, A1, . Location in patent: Page/Page column 31
[3] Patent: WO2004/87646, 2004, A2, . Location in patent: Page/Page column 112
[4] Patent: WO2006/34789, 2006, A1, . Location in patent: Page/Page column 41
  • 2
  • [ 142-08-5 ]
  • [ 540-37-4 ]
  • [ 13143-47-0 ]
YieldReaction ConditionsOperation in experiment
95% With 8-quinolinol; potassium carbonate In N,N-dimethyl-formamideInert atmosphere; Reflux; Large scale In a 3000L reactor, iodoaniline 438kg, 2-hydroxypyridine 190kg, 8-hydroxyquinoline 58kg, potassium carbonate 207kg, N,N-dimethylformamide (DMF) 1500kg, nitrogen protection, stirring is turned on. The mixture was warmed to reflux and reacted overnight. Chromatography was followed up to the end of the reaction. The potassium iodide was removed by filtration. Part of the DMF was recovered under reduced pressure, cooled to 50° C., and filtered to give crude 1-(4-aminophenyl)-1H-pyridin-2-one. The crude product was added with 740 kg of ethanol, heated and dissolved, and 55 kg of activated carbon was added for decoloration. The solution was filtered while hot, and the filtrate was cooled and crystallized. The product was filtered, dried and packaged to give 1-(4-aminophenyl)-1H-pyridin-2-one with a yield of 95. percent,The purity is 99percent.
70% With copper(l) iodide; 8-quinolinol; caesium carbonate In 1,4-dioxane; dimethyl sulfoxide at 120℃; for 15 h; Sealed tube 11128] In a similar manner as described in Example 114,(R)-5-(3-(4-methoxybenzamido)piperidin- 1 -yl)-3-(4-(2-ox-opyridin- 1 (2H)-yl)phenylamino)pyrazine-2-carboxamide(154) was prepared using 1 -(4-aminophenyl)pyridin-2(1H)-one. MS found for C29H29N704 as (M+H) 540.1, (M—H)538.3. UV: X=260, 285, 308, 346, 369 nm Synthesis of i-(4-aminophenyl)pyridin-2(1H)-one: The mixture of 4-iodoa-niline (1.00 g, 4.56 mmol), 2-hydroxypyridine (650 mg, 6.84mmol), fine powder Cs2CO3 (2.97 g, 9.12 mmol), fine powderCul (180mg, 0.92 mmol), 8-hydroxyquinoline (140mg, 0.92mmol) in 6 mE DMSO and 10 mE dioxane was stirred in asealed tube at 120° C. for 15 h. The mixture was diluted with300 mE EtOAc, filtered through celite, washed with brine,dried, concentrated and subjected to flash column with 0 to7percent MeOR in dichioromethane to isolate this compound (590mg, yield 70percent).
53.45% With copper(l) iodide; 8-quinolinol; potassium carbonate In dimethyl sulfoxide at 130℃; for 12 h; Inert atmosphere General procedure: Compound 1 (5g, 22.83mmol) was dissolved in DMSO (120mL), followed by the addition of 2-Piperidinone (4.53g, 45.66mmol), CuI (0.43g, 2.28mmol), 8-hydroxy-quinoline (0.66g, 4.57mmol) and K2CO3 (9.46g, 68.49mmol). The mixture was heated to 130°C under N2 for 12h, cooled, and quenched with water (120mL). The organics were extracted with ethyl acetate (2×150mL) and dried (Na2SO4). Purification by silica gel column chromatography (n-hexane/ethyl acetate, 5/1 to 3/1, as eluent) afforded compound 2 as faint yellow (2.80g, 64.47percent).
39.8% With copper(l) iodide; 8-quinolinol; caesium carbonate In dimethyl sulfoxide at 120℃; A mixture of pyridin-2-ol (2.00 g, 21.0 mmol), 4-iodoaniline (4.61 g, 21.0 mmol), 8-quinolinol (0.61 g, 4.2 mmol), Cul (0.80 g, 4.2 mmol) and Cs2C03 (10.26 g, 31.5 mmol) in DMSO (50 mL) was stirred at 120°C for overnight. After filtration, the filtrate was partitioned between EA and water and the aqueous layer was further extracted with EA. The combined organic layers was washed with water and brine, dried over anhydrous sodium sulfate and concentrated to afford the title compound as a green solid (1.56 g, 39.8 percent yield). MS (m/z): 186.9 (M+H)+.
39.8% With copper(l) iodide; 8-quinolinol; caesium carbonate In dimethyl sulfoxide at 120℃; A mixture of pyridin-2-ol (2.00 g, 21.0 mmol), 4-iodoaniline (4.61 g, 21.0 mmol), 8-quinolinol (0.61 g, 4.2 mmol), Cul (0.80 g, 4.2 mmol) and Cs2C03 (10.26 g, 31.5 mmol) in DMSO (50 mL) was stirred at 120°C for overnight. After filtration, the filtrate was partitioned between EA and water and the aqueous layer was further extracted with EA. The combined organic layers was washed with water and brine, dried over anhydrous sodium sulfate and concentrated to afford the title compound as a green solid (1.56 g, 39.8 percent yield). MS (m/z): 186.9 (M+H)+.

Reference: [1] Patent: CN107382836, 2017, A, . Location in patent: Paragraph 0021; 0022
[2] Patent: US2015/158865, 2015, A1, . Location in patent: Paragraph 1127; 1128
[3] European Journal of Medicinal Chemistry, 2017, vol. 125, p. 411 - 422
[4] Patent: WO2014/139145, 2014, A1, . Location in patent: Page/Page column 37
[5] Patent: WO2014/139465, 2014, A1, . Location in patent: Page/Page column 38
[6] Patent: WO2006/55951, 2006, A2, . Location in patent: Page/Page column 59
[7] Patent: WO2008/86226, 2008, A2, . Location in patent: Page/Page column 123-124
[8] Patent: WO2005/32468, 2005, A2, . Location in patent: Page/Page column 158
[9] Patent: WO2006/63113, 2006, A2, . Location in patent: Page/Page column 118
[10] Patent: WO2006/63293, 2006, A2, . Location in patent: Page/Page column 48-49
[11] Patent: WO2005/32468, 2005, A2, . Location in patent: Page/Page column 158
  • 3
  • [ 142-08-5 ]
  • [ 13143-47-0 ]
Reference: [1] Patent: WO2014/135471, 2014, A1,
  • 4
  • [ 350-46-9 ]
  • [ 13143-47-0 ]
Reference: [1] Patent: WO2014/135471, 2014, A1,
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